CN103319660B - Hydrogenated multicomponent copolymerized petroleum resin and preparation method thereof - Google Patents
Hydrogenated multicomponent copolymerized petroleum resin and preparation method thereof Download PDFInfo
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- CN103319660B CN103319660B CN201210082116.5A CN201210082116A CN103319660B CN 103319660 B CN103319660 B CN 103319660B CN 201210082116 A CN201210082116 A CN 201210082116A CN 103319660 B CN103319660 B CN 103319660B
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Abstract
The invention relates to a preparation method for a hydrogenated multicomponent copolymerized petroleum resin. The preparation method comprises: adding an inert solvent, a cyclopentadiene derivative, an aliphatic conjugated diolefin, an aromatic olefin and a monoolefine into a high pressure reaction kettle to form a mixed liquid, replacing with nitrogen for 2-3 times, heating the mixed liquid, slowly heating to 200-280 DEG C, controlling the reaction kettle pressure of less than 3 MPa, under the condition, reacting for 3-20 hours, after finishing the reaction, and performing reduced pressure distillation to obtain a multicomponent copolymerized petroleum resin; dissolving the obtained multicomponent copolymerized petroleum resin in a saturated aliphatic alkane solvent, in the presence of a hydrogenation catalyst, performing a hydrogenation reaction, controlling the temperature of 200-300 DEG C and the pressure of 8-20 MPa, after finishing the reaction, and performing reduced pressure distillation to obtain the hydrogenated multicomponent copolymerized petroleum resin. The obtained hydrogenated multicomponent copolymerized petroleum resin has the advantages of low color number and high thermal stability. The preparation method is simple in process and low in cost, and is safe and reliable.
Description
Technical field
The invention belongs to petrochemical industry, especially a kind of hydrogenation Multicomponent copolymer petroleum resin and preparation method thereof.
Background technology
Petroleum resin are with the by product C5 in petroleum cracking process, and C9 cut is the low-molecular-weight thermoplastic resin of one that main raw material polymerization obtains.Petroleum resin can be divided into C5 petroleum resin by the difference of its raw material sources, i.e. aliphatic petroleum resin, its mainly with olefin cracking obtain C 5 fraction in m-pentadiene for main raw material; C9 petroleum resin, i.e. aromatic petroleum resin, its mainly with the aromatic olefin in C9 cut for main raw material; C5/C9 petroleum resin are the mixed poly-resins with C5 raw material and C9 raw material mixing post polymerization.Dicyclopentadiene petroleum resin is the resin made for main raw material with dicyclopentadiene in C 5 fraction.Petroleum resin have the advantages such as reasonable price, water-fast, chemicals-resistant due to it, can be widely used in multiple industry and the fields such as rubber, tackiness agent, coating, papermaking, ink.The U.S. has just achieved the industrialization of petroleum resin as far back as the mid-40.Along with the development of petroleum industry, petroleum resin obtain in China and develop rapidly, and its production technology reaches its maturity, and have suitable industrial scale.
The production of petroleum resin is generally obtained by two kinds of methods, and one is catalytic polymerization.Method that catalyzed polymerization is commonly called as " cold poly-" is having catalyzer, as AlCl
3or BF
3deposit in case, under certain temperature of reaction, carry out polyreaction, form corresponding petroleum resin.Owing to there being the use of catalyzer, relatively complicated in the process of aftertreatment, easily bring corresponding pollution, therefore produce heavier environmental pressure.
Another kind is the method adopting thermopolymerization.Thermopolymerization, mainly for a kind of polymerization process taking dicyclopentadiene as main raw material, is by under higher temperature condition and pressure, and initiated polymerization forms the lower oligomer of molecular weight.Owing to not having the introducing of catalyzer, aftertreatment can not produce the environmental pollution brought by catalyst removal process, therefore, has environmental protection, and the superiority not containing any catalyst impurities in product.
Petroleum resin are polymerized by unsaturated olefin, molecular chain has the existence of a large amount of unsaturated double-bond, cause resin under the environment such as light and heat photograph, have unstable shortcoming, the chromophore that building-up process produces simultaneously can bring darker look number to rosin products.Due to the existence of above-mentioned defect, make petroleum resin without hydrotreatment in health care, the high-end applications such as food product pack are very restricted.How carrying out hydrotreatment to hot petroleum resin resin, more shallow to obtain color, more stable hydrogenation resin is the problem that industry is paid close attention to always.
At present, the hot polymerization petroleum resin solvability of produced in conventional processes and consistency are all poor, are especially insoluble in Aliphatic hydrocarbon solvents, directly affects the deep processing to petroleum resin, can not carry out hydrotreatment.
Summary of the invention
The object of the invention is to overcome the deficiencies in the prior art, provide a kind of preparation method of hydrogenation Multicomponent copolymer petroleum resin, the method technique is simple, cost is lower, and the resin of acquisition has good solubility and consistency, and good thermostability.
Another object of the present invention is to provide a kind of hydrogenation Multicomponent copolymer petroleum resin utilizing the preparation method of hydrogenation Multicomponent copolymer petroleum resin to make.
The present invention solves its technical problem and is achieved through the following technical solutions:
A kind of preparation method of hydrogenation Multicomponent copolymer petroleum resin, it adds inert solvent, cyclopentadiene derivant by ratio of weight and the number of copies in autoclave, aliphatics conjugated diolefin, aromatic olefin and monoolefine form mixed solution, nitrogen replacement 2-3 time, mixed solution is heated, slowly be warming up to 200-280 DEG C, in reactor, pressure-controlling is being less than 3MPa, reacts 3-20 hour under this condition, through underpressure distillation after reaction terminates, obtain Multicomponent copolymer petroleum resin;
The Multicomponent copolymer petroleum resin of acquisition is dissolved in Saturated alkane solvent, under the existence of hydrogenation catalyst, carry out hydrogenation reaction, the temperature of hydrogenation reaction controls at 200-300 DEG C, the pressure-controlling of hydrogenation reaction is at 8-20MPa, after question response terminates, obtain hydrogenation Multicomponent copolymer petroleum resin through underpressure distillation.
And the ratio of weight and number of each component of described formation mixed solution is:
Inert solvent 20-60 part;
Cyclopentadiene derivant 10-70 part;
Aliphatics conjugated diolefin 10-50 part;
Aromatic olefin 1-30 part;
Monoolefine 1-30 part.
And weight ratio is 1: 1-1: 4 between described Multicomponent copolymer petroleum resin and Saturated alkane solvent; Ratio between Multicomponent copolymer petroleum resin and hydrogenation catalyst is 50: 1-1000: 1.
And described cyclopentadiene derivant is one or more the mixture in dicyclopentadiene, methyldicyclopentadiene, norbornylene.
And described aromatic olefin is one or more the mixture in vinylbenzene, vinyl toluene, α-methylstyrene, indenes, methyl indenes.
And described aliphatics conjugated diolefin is one or more the mixture in divinyl, m-pentadiene, isoprene.
And described monoolefine is iso-butylene, isopentene, positive amylene, cyclopentenes one or more mixture wherein.
And described inert solvent is one or more the mixture in benzene,toluene,xylene, trimethylbenzene, hexane, hexanaphthene, heptane, octane, nonane, certain herbaceous plants with big flowers alkane, hendecane, 12 carbon alkane, No. 100 solvent oils, No. 200 solvent oils, solvent D40, solvent D60.
And described hydrogenation catalyst is made up of one or more in nickel, palladium, tungsten, copper, zinc, platinum.
And described Saturated alkane solvent is one or more the mixture in hexane, hexanaphthene, heptane, octane, nonane, certain herbaceous plants with big flowers alkane, hendecane, 12 carbon alkane, No. 100 solvent oils, No. 200 solvent oils, solvent oil D40, solvent oil D60.
And described hydrogenation reaction adopts still reaction, adopt the temperature of still reaction to control at 200-300 DEG C, pressure-controlling is at 8-20MPa, and the reaction times is 4-20 hour; Or hydrogenation reaction adopts fixed bed reaction, adopt the temperature of fixed bed reaction to control at 200-300 DEG C, pressure-controlling is at 8-20MPa, and the air speed of reaction is: 0.4-2hr
-1.
A kind of hydrogenation Multicomponent copolymer petroleum resin utilizing the preparation method of hydrogenation Multicomponent copolymer petroleum resin to prepare.
And the softening temperature of this hydrogenation Multicomponent copolymer petroleum resin is 70-150 DEG C, Gardner Color 0-2, weight-average molecular weight 400-1200, molecular weight distribution 1.5-3.2.
Advantage of the present invention and beneficial effect are:
1, the preparation method of this hydrogenation Multicomponent copolymer petroleum resin adds inert solvent, cyclopentadiene derivant, aliphatics conjugated diolefin by ratio of weight and the number of copies in autoclave, aromatic olefin and monoolefine form mixed solution, nitrogen replacement 2-3 time, mixed solution is heated, slowly be warming up to 200-280 DEG C, in reactor, pressure-controlling is being less than 3MPa, reacts 3-20 hour under this condition, through underpressure distillation after reaction terminates, obtain Multicomponent copolymer petroleum resin; The Multicomponent copolymer petroleum resin of acquisition is dissolved in Saturated alkane solvent, under the existence of hydrogenation catalyst, carry out hydrogenation reaction, the temperature of hydrogenation reaction controls at 200-300 DEG C, the pressure-controlling of hydrogenation reaction is at 8-20MPa, after question response terminates, hydrogenation Multicomponent copolymer petroleum resin is obtained through underpressure distillation, present method have employed the method for multi-component copolymer, by the change of the ratio of different sorts alkene, regulate the physicochemical property of the resin obtained, make the petroleum resin produced have better solvability and consistency.Especially the Multicomponent copolymer petroleum resin in the present invention has extraordinary solvability in aliphatic solvent, can carry out hydrotreatment.
2, present invention process is simple, cost is lower, and the hydrogenation Multicomponent copolymer petroleum resin of acquisition has the high advantage of stability of light color, is a kind of preparation method of safe and reliable hydrogenation Multicomponent copolymer petroleum resin.
Embodiment
Below by specific embodiment, the invention will be further described, and following examples are descriptive, is not determinate, can not limit protection scope of the present invention with this.
In the present invention, inert solvent, cyclopentadiene derivant, aliphatics conjugated diolefin, aromatic olefin, monoolefine, hydrogenation catalyst, saturated fatty hydrocarbon solvent all commercially can be bought and obtain.
Embodiment 1
A kind of preparation method of Multicomponent copolymer petroleum resin, inert solvent 200g is added by ratio of weight and the number of copies in autoclave, the present embodiment inert solvent adopts toluene, cyclopentadiene derivant 200g, the present embodiment cyclopentadiene derivant adopts dicyclopentadiene, aliphatics conjugated diolefin 100g, the present embodiment aliphatics conjugated diolefin adopts divinyl, aromatic olefin 100g, the present embodiment aromatic olefin adopts vinylbenzene, monoolefine 100g, the present embodiment monoolefine adopts iso-butylene to form mixed solution, nitrogen replacement 2 times, mixed solution is heated, slowly be warming up to 200 DEG C, in reactor, pressure-controlling is being less than 3MPa, react 20 hours under this condition, through underpressure distillation after reaction terminates, obtain Multicomponent copolymer petroleum resin,
By obtain the molten 600g of Multicomponent copolymer petroleum resin 300g in saturated fatty hydrocarbon solvent, the present embodiment Saturated alkane solvent adopts hexanaphthene, under the existence of 1g hydrogenation catalyst, carry out hydrogenation reaction, the present embodiment hydrogenation catalyst adopts nickel catalyzator (Ni5338P), and the temperature of hydrogenation reaction controls at 200 DEG C, and the pressure-controlling of hydrogenation reaction is at 8MPa, after question response terminates, obtain hydrogenation Multicomponent copolymer petroleum resin through underpressure distillation.In hydrogenation reaction, adopt still reaction, the reaction times is 8 hours; Also can adopt fixed bed reaction, the air speed of employing fixed bed reaction is: 1hr
-1.
A kind of hydrogenation Multicomponent copolymer petroleum resin utilizing the preparation method of hydrogenation Multicomponent copolymer petroleum resin to prepare.The softening temperature of this hydrogenation Multicomponent copolymer petroleum resin is 76 DEG C, Gardner Color 0, weight-average molecular weight 414, molecular weight distribution 1.8.
Aromatic olefin in the present embodiment can also adopt one or more the mixture in vinyl toluene, α-methylstyrene, indenes, methyl indenes, and this two or more mixture is the mixing of weight arbitrary proportion.Aliphatics conjugated diolefin can also adopt one or more the mixture in m-pentadiene, isoprene, and this two or more mixture is the mixing of weight arbitrary proportion.Monoolefine can also adopt isopentene, positive amylene, cyclopentenes one or more mixture wherein, and this two or more mixture is the mixing of weight arbitrary proportion.Inert solvent can also adopt one or more the mixture in toluene, dimethylbenzene, trimethylbenzene, hexane, hexanaphthene, heptane, octane, nonane, certain herbaceous plants with big flowers alkane, hendecane, 12 carbon alkane, No. 100 solvent oils, No. 200 solvent oils, solvent D40, solvent D60, and this two or more mixture is the mixing of weight arbitrary proportion.Cyclopentadiene derivant can also replace with one or more the mixture in methyldicyclopentadiene, norbornylene, and this two or more mixture is the mixing of weight arbitrary proportion.Hydrogenation catalyst can also be one or more mixtures in palladium, tungsten, copper, zinc, platinum, and this two or more mixture is the mixing of weight arbitrary proportion; Saturated alkane solvent can also be one or more the mixture in hexanaphthene, heptane, octane, nonane, certain herbaceous plants with big flowers alkane, hendecane, 12 carbon alkane, No. 100 solvent oils, No. 200 solvent oils, solvent oil D40, solvent oil D60, and this two or more mixture is the mixing of weight arbitrary proportion.
Embodiment 2
A kind of preparation method of hydrogenation Multicomponent copolymer petroleum resin, inert solvent 600g is added by ratio of weight and the number of copies in autoclave, the present embodiment inert solvent adopts No. 200 solvent oils, cyclopentadiene derivant 700g, the present embodiment cyclopentadiene derivant is methyldicyclopentadiene, aliphatics conjugated diolefin 500g, the present embodiment aliphatics conjugated diolefin is m-pentadiene, aromatic olefin 300g, the present embodiment aromatic olefin is vinyl toluene, monoolefine 300g, the present embodiment monoolefine is isopentene, form mixed solution, nitrogen replacement 3 times, mixed solution is heated, slowly be warming up to 280 DEG C, in reactor, pressure-controlling is at 3MPa, react 3 hours under this condition, through underpressure distillation after reaction terminates, obtain Multicomponent copolymer petroleum resin,
The Multicomponent copolymer petroleum resin 300g of acquisition is dissolved in Saturated alkane solvent 600g, under the catalysis of 3g palladium catalyst, carry out hydrogenation reaction, the temperature of hydrogenation reaction controls at 300 DEG C, the pressure-controlling of hydrogenation reaction is at 20MPa, after question response terminates, obtain hydrogenation Multicomponent copolymer petroleum resin through underpressure distillation.
A kind of hydrogenation Multicomponent copolymer petroleum resin utilizing the preparation method of hydrogenation Multicomponent copolymer petroleum resin to prepare.The softening temperature of this hydrogenation Multicomponent copolymer petroleum resin is 119 DEG C, Gardner Color 2, weight-average molecular weight 1135, molecular weight distribution 3.2.
Embodiment 3
A kind of preparation method of hydrogenation Multicomponent copolymer petroleum resin, inert solvent 400g is added by ratio of weight and the number of copies in autoclave, the present embodiment inert solvent adopts solvent D40 and nonane weight ratio to be the mixture of 1: 1, cyclopentadiene derivant 400g, the present embodiment cyclopentadiene derivant is that between methyldicyclopentadiene and norbornylene, weight ratio is the mixture of 3: 1, aliphatics conjugated diolefin 300g, the present embodiment aliphatics conjugated diolefin adopts weight ratio between isoprene and m-pentadiene to be the mixture of 1: 2, aromatic olefin 160g, the present embodiment aromatic olefin adopts weight ratio between α-methylstyrene and methyl indenes to be the mixture of 2: 1, monoolefine 150g, the present embodiment monoolefine adopts weight ratio between amylene and cyclopentenes to be the mixture of 1: 1, form mixed solution, nitrogen replacement 3 times, mixed solution is heated, slowly be warming up to 240 DEG C, in reactor, pressure-controlling is being less than 3MPa, react 12 hours under this condition, through underpressure distillation after reaction terminates, obtain Multicomponent copolymer petroleum resin,
The Multicomponent copolymer petroleum resin 300g of acquisition is dissolved in octane, 12 carbon alkane, solvent oil D40 according in 1: 1: 1 weight proportion 600g, according under the existence of the catalyzer 6g of 1: 1: 1 weight proportion formation between nickel, zinc, platinum, carry out hydrogenation reaction, the temperature of hydrogenation reaction controls at 250 DEG C, the pressure-controlling of hydrogenation reaction is at 14MPa, after question response terminates, obtain hydrogenation Multicomponent copolymer petroleum resin through underpressure distillation.
A kind of hydrogenation Multicomponent copolymer petroleum resin utilizing the preparation method of hydrogenation Multicomponent copolymer petroleum resin to prepare.The softening temperature of this hydrogenation Multicomponent copolymer petroleum resin is 104 DEG C, Gardner Color 1, weight-average molecular weight 800, molecular weight distribution 2.4.
Multi-copolymerization resin owing to obtaining in the present invention has good solubility, for the further hydrogenation deep processing process of this resin provides possibility in aliphatic solvent.By the resin after hydrotreatment, due to the removal of double bond, there is light colour, the advantage of high stability.The look number of such as non-hydrogenation resin usually can at about 4-8, and the color of the resin after hydrotreatment can be reduced to less than No. 2, even can obtain water white No. 0 resin.The thermostability of the resin after hydrogenation and the resin-phase of non-hydrogenation are than also increasing significantly.The resin of such as non-hydrogenation was 160 DEG C of insulations 12 hours, and look number can raise more than 5 units.Through the multi-copolymerization resin of hydrotreatment, under corresponding condition, look rising can not more than 2 units.The hydrogenation multi-copolymerization resin obtained in the present invention, owing to having above-mentioned advantage, can be applied to health care, and food product pack etc. require harsher high-end field.With the resin-phase of non-hydrogenation than greatly having expanded the range of application of resin.
Claims (11)
1. the preparation method of a hydrogenation Multicomponent copolymer petroleum resin, it is characterized in that: in autoclave, add inert solvent, cyclopentadiene derivant, aliphatics conjugated diolefin by ratio of weight and the number of copies, aromatic olefin and monoolefine form mixed solution, nitrogen replacement 2-3 time, heats mixed solution, is slowly warming up to 200-280 DEG C, in reactor, pressure-controlling is being less than 3MPa, react 3-20 hour under this condition, through underpressure distillation after reaction terminates, obtain Multicomponent copolymer petroleum resin;
The Multicomponent copolymer petroleum resin of acquisition is dissolved in Saturated alkane solvent, under the existence of hydrogenation catalyst, carry out hydrogenation reaction, the temperature of hydrogenation reaction controls at 200-300 DEG C, the pressure-controlling of hydrogenation reaction is at 8-20MPa, after question response terminates, obtain hydrogenation Multicomponent copolymer petroleum resin through underpressure distillation, the ratio of weight and number of each component of described formation mixed solution is:
described cyclopentadiene derivant is one or more the mixture in dicyclopentadiene, methyldicyclopentadiene, norbornylene.
2. the preparation method of hydrogenation Multicomponent copolymer petroleum resin according to claim 1, is characterized in that: between described Multicomponent copolymer petroleum resin and Saturated alkane solvent, weight ratio is 1:1-1:4; Ratio between Multicomponent copolymer petroleum resin and hydrogenation catalyst is 50:1-1000:1.
3. the preparation method of hydrogenation Multicomponent copolymer petroleum resin according to claim 1, is characterized in that: described aromatic olefin is one or more the mixture in vinylbenzene, vinyl toluene, α-methylstyrene, indenes, methyl indenes.
4. the preparation method of hydrogenation Multicomponent copolymer petroleum resin according to claim 1, is characterized in that: described aliphatics conjugated diolefin is one or more the mixture in divinyl, m-pentadiene, isoprene.
5. the preparation method of hydrogenation Multicomponent copolymer petroleum resin according to claim 1, is characterized in that: described monoolefine is iso-butylene, isopentene, positive amylene, cyclopentenes one or more mixture wherein.
6. according to the preparation method of the hydrogenation Multicomponent copolymer petroleum resin described in claim 1, it is characterized in that: described inert solvent is one or more the mixture in benzene,toluene,xylene, trimethylbenzene, hexane, hexanaphthene, heptane, octane, nonane, certain herbaceous plants with big flowers alkane, hendecane, 12 carbon alkane, No. 100 solvent oils, No. 200 solvent oils, solvent D40, solvent D60.
7. according to the preparation method of the hydrogenation Multicomponent copolymer petroleum resin described in claim 1, it is characterized in that: described hydrogenation catalyst is made up of one or more in nickel, palladium, tungsten, copper, zinc, platinum.
8. according to the preparation method of the hydrogenation Multicomponent copolymer petroleum resin described in claim 1, it is characterized in that: described Saturated alkane solvent is one or more the mixture in hexane, hexanaphthene, heptane, octane, nonane, certain herbaceous plants with big flowers alkane, hendecane, 12 carbon alkane, No. 100 solvent oils, No. 200 solvent oils, solvent oil D40, solvent oil D60.
9. according to the preparation method of the hydrogenation Multicomponent copolymer petroleum resin described in claim 1, it is characterized in that: described hydrogenation reaction adopts still reaction, adopt the temperature of still reaction to control at 200-300 DEG C, pressure-controlling is at 8-20MPa, and the reaction times is 4-20 hour; Or hydrogenation reaction adopts fixed bed reaction, adopt the temperature of fixed bed reaction to control at 200-300 DEG C, pressure-controlling is at 8-20MPa, and the air speed of reaction is: 0.4-2hr
-1.
10. the hydrogenation Multicomponent copolymer petroleum resin prepared of a preparation method as claimed in claim 1.
11., according to the hydrogenation Multicomponent copolymer petroleum resin described in claim 10, is characterized in that: the softening temperature of this hydrogenation Multicomponent copolymer petroleum resin is 70-150 DEG C, Gardner Color 0-2, weight-average molecular weight 400-1200, molecular weight distribution 1.5-3.2.
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| CN104945560B (en) * | 2015-06-29 | 2017-11-21 | 安徽同心化工有限公司 | A kind of phenylethene modified dicyclopentadiene petroleum resin of hydrogenation and preparation method thereof |
| CN108239224B (en) * | 2018-01-10 | 2021-03-23 | 安徽同心新材料科技有限公司 | High-performance copolymer resin product for producing tire tread rubber and preparation method thereof |
| CN108795214A (en) * | 2018-07-04 | 2018-11-13 | 濮阳市瑞森石油树脂有限公司 | A kind of hot-melt type pavement strip paint |
| KR102155698B1 (en) * | 2019-12-17 | 2020-09-14 | 코오롱인더스트리 주식회사 | Hydrogenated petroleum resin and rubber composition comprising the same |
| CN113717486B (en) * | 2021-09-17 | 2022-09-02 | 恒河材料科技股份有限公司 | Preparation method of BOPP film stiffening agent |
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